Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$7,000
28
29
30
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
7
8
9
10
11
$10,000
12
13
14
15
16
17
18
$10,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
31
 $15,000
August 2026
SuMoTuWeThFrSaWeek
 1
$15,000
2
3
4
5
6
7
8
$17,000
9
10
11
12
13
14
15
$17,000
16
17
18
19
20
21
22
$12,000
23
24
25
26
27
28
29
$10,000
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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Stunning New Custom Luxury Home, Oak Bluffs, 18 x 36 Heated Saltwater Pool, Bluestone Patio, 4 Bedrooms 3.5 baths

Tucked just beyond the heart of downtown Oak Bluffs, this spacious, architect-designed retreat offers families and friends an exceptional Vineyard vacation experience.

Thoughtfully crafted by a noted architect, the home...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$8,500 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,500
7
8
9
10
11
12
13
$8,500
14
15
16
17
18
19
20
$11,000
21
22
23
24
25
26
27
$14,000
28
29
30
 $16,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$16,500
5
6
7
8
9
10
11
$16,500
12
13
14
15
16
17
18
$18,000
19
20
21
22
23
24
25
$18,000
26
27
28
29
30
31
 $20,000
August 2026
SuMoTuWeThFrSaWeek
 1
$20,000
2
3
4
5
6
7
8
$20,000
9
10
11
12
13
14
15
$21,000
16
17
18
19
20
21
22
$21,500
23
24
25
26
27
28
29
$18,000
30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$9,000
27
28
29
30
 $9,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

1st Two Weeks of July 2026 being offered at $16,500 per week

 

Pool Heated to 81 degrees July & August included in Rental Rate

Pool Heated to 81 degrees June & September additional $300 Propane Surcharge

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Lovely Oak Bluffs Escape, 3 Bedrooms in Main House, 2 Bedrooms over Garage, 3.5 Baths Multiple Living Spaces, Walk to Oak Bluffs Center, 1 Mile

Nestled on a tranquil cul-de-sac in the heart of Oak Bluffs, this meticulously renovated Modern Colonial offers a special Martha's Vineyard experience. Thoughtfully reimagined in 2025, the property encompasses a...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$70 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$8,400
28
29
30
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
7
8
9
10
11
$9,000
12
13
14
15
16
17
18
$9,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$14,000
16
17
18
19
20
21
22
$12,000
23
24
25
26
27
28
29
$10,000
30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
 $7,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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Lovely, Newly Updated Oak Bluffs Home. Multiple Indoor/Outdoor Living/Lounge Areas, Sleeps 8, 10/15 minute Walk to the Vilage Center.

Note: All photos are virtually staged photos by the owner, all new furnishings will be arriving throughout the winter months. 

Welcome to Noble House, a beautifully updated home nestled in a charming neighborhood just...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
3
Baths: 
2
Price Range:
$4,500 - $8,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$7,200
21
22
23
24
25
26
27
$7,200
28
29
30
 $7,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,700
5
6
7
8
9
10
11
$7,700
12
13
14
15
16
17
18
$7,700
19
20
21
22
23
24
25
$7,700
26
27
28
29
30
31
 $9,000
August 2026
SuMoTuWeThFrSaWeek
 1
$9,000
2
3
4
5
6
7
8
$9,000
9
10
11
12
13
14
15
$9,000
16
17
18
19
20
21
22
$8,500
23
24
25
26
27
28
29
$8,800
30
31
 $8,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,200
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$6,000 - $8,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$7,500
28
29
30
 $8,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$9,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
18
19
20
21
22
$12,000
23
24
25
26
27
28
29
$8,500
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $6,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $8,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,500
28
29
30
 $8,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$9,000
26
27
28
29
30
31
 $9,000
August 2026
SuMoTuWeThFrSaWeek
 1
$9,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
18
19
20
21
22
$11,500
23
24
25
26
27
28
29
$9,000
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $6,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Lovely Custom Contemporary Home, Tucked in the Community of Bayes Hill, 4 Bedrooms, 4 Bath, Landscaped, Deck, Patio Dining Area

Designed with a sophisticated contemporary aesthetic, this chic vacation retreat showcases an open floor plan, expansive windows, and beautifully curated interiors. Offering four bedrooms and 3.5 baths, the home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $8,050
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,500
7
8
9
10
11
12
13
$7,500
14
15
16
17
18
19
20
$7,500
21
22
23
24
25
26
27
$7,500
28
29
30
 $7,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,750
5
6
7
8
9
10
11
$7,750
12
13
14
15
16
17
18
$7,750
19
20
21
22
23
24
25
$7,750
26
27
28
29
30
31
 $8,050
August 2026
SuMoTuWeThFrSaWeek
 1
$8,050
2
3
4
5
6
7
8
$8,050
9
10
11
12
13
14
15
$8,050
16
17
18
19
20
21
22
$8,050
23
24
25
26
27
28
29
$8,050
30
31
 $8,050
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,050
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $7,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Auto Ferry Ticket available for Purchase 7/19 - 7/26. Please inquire!  (mv)

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Summer Wind in the Heart of Oak Bluffs, Water views. 2 minute Walk to Inkwell Beach & 5 minute walk to town, All Newly Remodeled 5 Bedroom, 3 Bath Home With Deluxe Amenities

Set in the heart of Oak Bluffs center, this newly renovated home features water views, walk to Inkwell Beach and Pay Beach and walk to the town center all within...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$8,000 - $8,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$9,000
21
22
23
24
25
26
27
$10,000
28
29
30
 $12,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,000
5
6
7
8
9
10
11
$12,000
12
13
14
15
16
17
18
$13,000
19
20
21
22
23
24
25
$14,000
26
27
28
29
30
31
 $14,000
August 2026
SuMoTuWeThFrSaWeek
 1
$14,000
2
3
4
5
6
7
8
$19,000
9
10
11
12
13
14
15
$19,000
16
17
18
19
20
21
22
$19,000
23
24
25
26
27
28
29
$12,000
30
31
 $9,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$550
Tax: State & Local: 
11.7

Ferry tickets available for purchase, 7/26 - 8/2  Please inquire   (mv)

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Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,500 - $8,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
 $6,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
31
 $7,000
August 2026
SuMoTuWeThFrSaWeek
 1
$7,000
2
3
4
5
6
7
8
$8,000
9
10
11
12
13
14
15
$8,000
16
17
18
19
20
21
22
$8,000
23
24
25
26
27
28
29
$8,000
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $4,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Ferry Tickets Available 6/27-7/4, 7/4-7/11, 7/18-7/25 - please inquire

 

Note: Owner maintains security camera on front of house

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Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$7,950 - $7,950
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 $7,950
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,950
5
6
7
8
9
10
11
$7,950
12
13
14
15
16
17
18
$7,950
19
20
21
22
23
24
25
26
27
28
29
30
31
 $8,250
August 2026
SuMoTuWeThFrSaWeek
 1
$8,250
2
3
4
5
6
7
8
$8,500
9
10
11
12
13
14
15
$8,500
16
17
18
19
20
21
22
$8,500
23
24
25
26
27
28
29
$8,250
30
31
 
September 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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Lovely Home, Centrally Located, Bike Paths, AC all Rooms

This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window AC in all rooms, and a well-equipped modern kitchen. The home is nicely situated...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$7,500 - $7,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$7,500
28
29
30
 $7,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,500
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$7,500
19
20
21
22
23
24
25
$7,500
26
27
28
29
30
31
 $7,500
August 2026
SuMoTuWeThFrSaWeek
 1
$7,500
2
3
4
5
6
7
8
$7,800
9
10
11
12
13
14
15
$7,800
16
17
18
19
20
21
22
$7,800
23
24
25
26
27
28
29
$7,800
30
31
 
September 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,250 - $7,750
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,750
7
8
9
10
11
12
13
$5,750
14
15
16
17
18
19
20
$5,750
21
22
23
24
25
26
27
$7,000
28
29
30
 $9,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,750
5
6
7
8
9
10
11
$9,750
12
13
14
15
16
17
18
$9,750
19
20
21
22
23
24
25
$9,750
26
27
28
29
30
31
 $11,000
August 2026
SuMoTuWeThFrSaWeek
 1
$11,000
2
3
4
5
6
7
8
$11,000
9
10
11
12
13
14
15
$11,000
16
17
18
19
20
21
22
$11,000
23
24
25
26
27
28
29
$11,000
30
31
 $7,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,750
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$6,900
20
21
22
23
24
25
26
$6,800
27
28
29
30
 $6,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
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Beautiful East Chop Home , Walk to Town & Beach, Outdoor Patio Area with Patio Dining

 Lovely Spacious East Chop Area home features elegant custom craftsmanship throughout, a light-filled open kitchen, living and dining areas, and a family/TV room. 3 bedrooms on the 2nd level and 2...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,500 - $7,500
June 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$7,500
9
10
11
12
13
14
15
$7,500
16
17
18
19
20
21
22
$7,500
23
24
25
26
27
28
29
30
31
 
September 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Auto Ferry tickets for purchase, 7/11 & 7/18 weeks. Inquire for Details (mv)

 

July Rates Recently Reduced by $1500, See Calendar for current rates. 

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Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$4,000 - $7,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$5,600
28
29
30
 $7,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,500
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$8,500
9
10
11
12
13
14
15
$8,500
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
Add Favorite
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Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$6,800 - $7,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,800
7
8
9
10
11
12
13
$6,800
14
15
16
17
18
19
20
$6,800
21
22
23
24
25
26
27
$6,800
28
29
30
 $6,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,900
5
6
7
8
9
10
11
$6,900
12
13
14
15
16
17
18
$6,900
19
20
21
22
23
24
25
$6,900
26
27
28
29
30
31
 $6,900
August 2026
SuMoTuWeThFrSaWeek
 1
$6,900
2
3
4
5
6
7
8
$7,900
9
10
11
12
13
14
15
$7,900
16
17
18
19
20
21
22
$7,900
23
24
25
26
27
28
29
$7,900
30
31
 $7,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,200
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

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